Things to Do in Winnipeg in May – 2026

Things to Do in Winnipeg in May: Events, Activities, and Festivals happening in Winnipeg during May 2026.

 
03 Jun

FortWhyte Alive, 1961 McCreary Road, Winnipeg

June 3, 2025 To September 3, 2026

$16.50 - $22

Spend an evening paddling before sunset for the perfect summer night. Paddle Nights are a 40-minute session with a canoe or kayak, with help available to get ...  »

07 Mar

FortWhyte Alive, 1961 McCreary Rd, Winnipeg

March 7, 2026 To April 3, 2027

(204) 989-8355

Free with regular admission

A line-up of inspired exploration to allow you to connect, learn, and explore our intrinsic connection with the natural world.  »

07 Mar

West End Cultural Centre, 586 Ellice Avenue, Winnipeg

March 7, 2026 To May 31, 2026

$20-$60plus service fees

03.07 Michael Kaeshammer*// Pop, Jazz, RB 03.15 Dust Rhinos St. Patrick’s Day* // Celtic Trad 03.19 Two Pianos, No Rodeo* //Blues, Singersongwriter, Piano forward Past and present Blue Rodeo pianists ...  »

14 Apr

Alloway Reception Centre- FortWhyte Alive, 1961 McCreary Road, Winnipeg

April 14, 2026 To May 28, 2026

Regular Admission

Get out on the trails in the early morning to experience the spring migration season. Enjoy this self-guided experience at your own pace and witness the abundance ...  »

16 Apr

The Berney Theatre, 123 Doncaster Street., Winnipeg

April 16, 2026 To May 2, 2026

204-477-7515

$30 to $55

The extraordinary story of the first woman to cycle around the world. Annie Londonderry set out to be the first woman to cycle around the world in 1894 ...  »

24 Apr

Black Box Theatre Pros, MTYP Black Box Theatre, 2 Forks Market Road, Winnipeg

April 24, 2026 To May 17, 2026

$25 - $28 + taxes and fees

Spirited Shizu and her serious father struggle to appreciate each other until the day she hides in her father’s suitcase and travels secretly to his most ...  »

29 Apr

John Hirsch Mainstage, 174 Market Ave, Winnipeg

April 29, 2026 To May 23, 2026

204 942 6537

$26.00 to $95.25

Métis singer-songwriter Andrea Menard's feast for the senses blends master storytelling with the beauty of Métis culture through music, dance and visual art.  »

30 Apr

Centennial Concert Hall, 555 Main Street, Winnipeg

April 30, 2026 To May 3, 2026

Price starts at $40

Celebrate the RWB’s past, present, and future with a powerful trio of ballets. This dynamic program features the return of James Kudelka’s masterwork The Four ...  »

01 May

Assiniboia Downs, 3975 Portage Avenue, Winnipeg

May 1, 2026 To May 24, 2026

$29.95 - $32

Get ready for over a month of excitement and family fun! Wonder Shows presents its annual "Family Fun Spring Fair"! Join us every weekend for a spectacular ...  »

01 May

Young United Church, 222 Furby Street, Winnipeg

May 1, 2026 To May 2, 2026

Varies

Celebrate the spirit and sound of the Canadian Prairies in this vibrant choral tribute to the music of Manitoba and beyond. Featuring new arrangements of songs by ...  »

01 May

Winnipeg Art Gallery, 300 Memorial Boulevard, Winnipeg

May 1, 2026 To August 7, 2026

$36.50 - $63.50 + fees

Candlelight concerts bring the magic of a live, multi-sensory musical experience to awe-inspiring locations like never seen before in Winnipeg. Get your tickets now to discover the ...  »

01 May

Winnipeg Art Gallery, 300 Memorial Boulevard, Winnipeg

May 1, 2026 To July 10, 2026

$36.50 - $65.50 + fees

Candlelight concerts bring the magic of a live, multi-sensory musical experience to awe-inspiring locations like never seen before in Winnipeg. Get your tickets now to discover the ...  »

02 May

Niverville Heritage Centre , 100C Heritage Trail Niverville

May 2, 2026

2043885000

By Monetary Donation

Join us as the Niverville Heritage Centre hosts the 2026 MB Makers Market–An Exclusive show featuring handmade items!  »

02 May

FortWhyte Farms, 1961 McCreary Road, Winnipeg

May 2, 2026

$120 - $140 + $65 Material Cost

Eric Gyselman will guide participants through the entire process of shaping a wooden canoe paddle, allowing you to create and take home your very own!  »

02 May

West End Cultural Centre, 586 Ellice Avenue, Winnipeg

May 2, 2026

Free, donations accepted

Bloom in the Dark is no ordinary market - it’s an after-dark gathering of mystery, creativity and beautifully strange delights. Step into a spellbound evening filled ...  »

05 May

Tom Hendry Warehouse, 140 Rupert Ave, Winnipeg

May 5, 2026 To May 9, 2026

$75 - $125

The Royal Manitoba Theatre Centre and the Manitoba Bar Association present Crazy For You at the Tom Hendry Warehouse. The annual Lawyers Play is one of Royal ...  »

06 May

Various locations, Winnipeg

May 6, 2026 To May 23, 2026

$13 + GST (25% off for Rady JCC Members)

See a programme of exceptional films from around the world (including premiere screenings) that encompass the joy, pain, humour, richness, and creativity of the Jewish experience.  »

07 May

Martial-Caron Theatre, 200 De La Cathedrale Ave, Winnipeg

May 7, 2026 To May 10, 2026

$25

“Miss Holmes”, by Christopher M. Walsh, based on characters by Sir Arthur Conan Doyle. Join Miss Sherlock Holmes and Dr. Dorothy Watson as they work together to ...  »

08 May

Morning Sound Farm, 43151 Rd 2 E, Sanford, MB

May 8, 2026 To August 8, 2026

$13 - $15

Experience a day in the country with milking, shearing, pony rides, hayrides and loads of face-to-face time with animals and farmers.  »

08 May

Young United Church, 222 Furby St #202, Winnipeg

May 8, 2026 To May 9, 2026

$40 plus fees

Join Prairie Voices for their annual dessert concert! Enjoy some sweet desserts while being serenaded by equally sweet choral music.  »

08 May

Knox United Church, 400 Edmonton Street, Winnipeg

May 8, 2026

$0.00 - $43.67

Spanning moods from intimacy to grandeur, renowned Manitoba-born violinist James Ehnes celebrates his 50th birthday with us in a solo recital, illuminating the delicate threads that run ...  »

08 May

The Forks Market, Winnipeg

May 8, 2026 To November 6, 2026

UnCommon Pours 2026 Full Package $158.66

UnCommon Pours is a four-part series celebrating exclusive beer and wine selections at The Common in The Forks Market. With two wine-focused and two beer-focused events spread ...  »

09 May

Exhibition Place at Red River Exhibition Park, 3977 Portage Ave, Winnipeg

May 9, 2026 To May 10, 2026

$8 - $12

Honour the Mother, mentor, or special someone in your life with a memorable day of hunting for unique treasures, making memories, and welcoming spring.   »

09 May

Centennial Concert Hall, 555 Main Street, Winnipeg

May 9, 2026 To May 10, 2026

$15.71 - $124 + taxes and fees

Written at the height of his compositional prowess (which is really saying something), the Clarinet Concerto in A Major is a work that is idiomatic and idiosyncratic. ...  »

09 May

Mennonite Heritage Village, 231 Provincial Trunk Hwy 12, Steinbach

May 9, 2026

2043269661

Free admission

Celebrate Manitoba Day at Mennonite Heritage Village! Join us as we celebrate Manitoba’s birthday with a day full of activities, history, and community fun! This special ...  »

09 May

Union Centre, 275 Broadway, Winnipeg

May 9, 2026

$55.00 (A partial tax receipt will be issued.)

Enjoy thrilling live performances by the Winnipeg Singers, paired with beautifully crafted canapés by Capital Grill and Bar, all in the heart of downtown Winnipeg.   »

09 May

Burton Cummings Theatre, 364 Smith St., Winnipeg

May 9, 2026

$78 - $90

Canada’s #1 stand-up road warrior Ron James, is in the driver’s seat once again and bound full throttle for the ‘big wide open’ with his new ...  »

09 May

Prairie Dog Central, 64099 Prairie Dog Trail, Winnipeg

May 9, 2026

$55

We’re accepting Rebellion and the Dark Side to join us on this journey! Join characters from the iconic franchise, along with special preboarding gifts for all ...  »

10 May

Prairie Dog Central, 64099 Prairie Dog Trail, Winnipeg

May 10, 2026

$50 to $55

Treat your Mom to a special day as we make our way from Inkster Junction Station to the rural community of Grosse Isle.  »

10 May

The Dalnavert Museum, 61 Carlton, Winnipeg

May 10, 2026 To September 6, 2026

204-898-4678

$30 - $37

Join us for a beginner-friendly watercolour tutorial, then relax in Dalnavert's beautiful garden with a mimosa while you create your plein-air masterpiece!   »

10 May

Winnipeg Art Gallery, 300 Memorial Blvd, Winnipeg

May 10, 2026 To December 13, 2026

2047866641

Free

Join us on the second Sunday of every month for free admission to WAG-Qaumajuq and more family fun, thanks to a special partnership with Canada Life.  »

10 May

Velvet Glove Restaurant - The Fairmont Winnipeg, 2 Place Lombard, Winnipeg

May 10, 2026

$0.00 - $119.00 per person

Fairmont Winnipeg invites you to enjoy time together amongst family and friends and celebrate the special woman in your life, over traditional favorites and inspired new food ...  »

10 May

Fort Garry Hotel, 222 Broadway, Winnipeg

May 10, 2026

$21.93

Lenny Chet Breau is a virtuoso of the guitar, and a veteran of the Manitoban music scene.  »

10 May

Burton Cummings Theatre, 364 Smith St., Winnipeg

May 10, 2026

$47 - $74

Sooshi Mango is an Australian comedy troupe founded in 2015. The group consists of two brothers, Joe and Carlo Salanitri, and their best friend, Andrew Manfre.  »

12 May

Assiniboia Downs, 3975 Portage Ave, Winnipeg

May 12, 2026 To August 25, 2026

Free

At Assiniboia Downs, we believe in making your racing experience unforgettable for the whole family! Enjoy free family fun events during live racing nights.  »

14 May

Owner Property, 387 Broadway Ave., Winnipeg

May 14, 2026

2049962326

Free

Pop Up Market coming to Broadway! Come shop for baked goods, food truck yummies, clothing, jewelry, toys, house decor, and more! We will be inside and outdoors. ...  »

14 May

387 Broadway Avenue, Winnipeg

May 14, 2026 To June 26, 2026

Free

Pop Up Market coming to Broadway! Come shop for baked goods, food truck yummies, clothing, jewelry, toys, house decor, and more! We will be inside and outdoors.  »

15 May

Hilton Winnipeg Airport Suites, 800 Wellington Ave, Winnipeg

May 15, 2026 To May 17, 2026

$50-90

Keycon is Manitoba’s longest running Science Fiction and Fantasy Convention.  »

15 May

Prairie Dog Central, 64099 Prairie Dog Trail, Winnipeg

May 15, 2026

$37.50

Kick off the 2026 Prairie Dog Central season with a unique Friday night charter. This opportunity to ride the train, visit Grosse Isle in a rare summer night ...  »

16 May

FortWhyte Alive, 1961 McCreary Road, Winnipeg

May 16, 2026 To May 17, 2026

General admission

Start the season off right by fishing for northern pike, yellow perch and carp on our lakes. You are welcome to bring your own fishing equipment or ...  »

16 May

Prairie Dog Central, 64099 Prairie Dog Trail, Winnipeg

May 16, 2026 To June 20, 2026

$45

The most famous Gangster Duo of all time has its sights set on the Prairie Dog Central! Join us as we band together to foil the heist ...  »

16 May

IKEA Winnipeg, 500 Sterling Lyon Parkway, Winnipeg

May 16, 2026 To May 17, 2026

Free

Spring is in the air, and so is the excitement! 🎉 Join us for Foodtrip Market SpringFest, a day full of blooming joy, delicious food, and local treasures  »

16 May

Burton Cummings Theatre, 364 Smith St, Winnipeg

May 16, 2026

$43 and up

Blippi is coming to Winnipeg in the all-new Be Like Blippi Tour!   »

16 May

Oak Hammock Marsh, 1 Snow Goose Bay, Stonewall

May 16, 2026 To May 18, 2026

Included with general admission

Explore the hidden world of wetlands with hands-on activities that will let participants investigate wildlife, monitor species, and uncover the science behind conservation.  »

17 May

Club Room -The Fort Garry Hotel, 222 Broadway, Winnipeg

May 17, 2026

$21.93

Originally from Toronto, Ontario, drummer Fabio Ragnelli is a JUNO Award-winning drummer and has been an in-demand sideman performing, recording, and touring with a number of artists ...  »

17 May

Fort Garry Hotel Concert Hall, 222 Broadway, Winnipeg

May 17, 2026 To July 31, 2026

$40 - $66.50

andlelight concerts bring the magic of a live, multi-sensory musical experience to awe-inspiring locations like never seen before in Winnipeg. Get your tickets now to discover the ...  »

17 May

The Velvet Glove, 2 Lombard Pl., Winnipeg

May 17, 2026 To June 21, 2026

$48.00 - $75.00 per person

Immerse yourself with our Mamma Mia! inspired Afternoon Tea experience, featuring an exquisite menu with iconic melodies.  »

17 May

Fort Garry Hotel Concert Hall, 222 Broadway, Winnipeg

May 17, 2026

$40.50 - $61 + fees

Candlelight concerts bring the magic of a live, multi-sensory musical experience to awe-inspiring locations like never seen before in Winnipeg. Get your tickets now to discover the ...  »

17 May

Prairie Dog Central, 64099 Prairie Dog Trail, Winnipeg

May 17, 2026

$55

Join Elsa, Moana, Rapunzel, Cinderella, Ariel, Fairy Godmother and Princess Charming for this magical experience on Sunday, May 17th aboard the Prairie Dog Central Railway  »

21 May

Neil Bardal Funeral Centre, 3030 Notre Dame Avenue, Winnipeg

May 21, 2026

$75 - $80

The Winnipeg Jazz Orchestra presents one of our most anticipated fundraisers, St. James Infirmary Blues. A Wonderful Evening of New Orleans inspired jazz and other soul music.  »

21 May

Dalnavert Museum and Visitors' Centre, 61 Carlton Street, Winnipeg

May 21, 2026

$120 for a group of 4

Step into the past at The Garden Party Mystery, an immersive, escape-room-style experience with a twist. Instead of breaking out, you’ll be sleuthing your way in, ...  »

22 May

Young United Church, 222 Furby St #202, Winnipeg

May 22, 2026 To May 23, 2026

TBA

It’s time for Horizon’s annual Lyrics & Lager concert! An evening of food, drinks, fun music and more. Don’t miss this fun event as it’...  »

23 May

Assiniboia Downs, 3975 Portage Avenue, Winnipeg

May 23, 2026 To May 24, 2026

$7 (5 & under free).

MB Food Truck Battles is back at Assiniboia Downs for a full weekend of incredible eats, live entertainment, and all your favourites in one place.  »

23 May

Prairie Dog Central, 64099 Prairie Dog Trail, Winnipeg

May 23, 2026 To June 27, 2026

$45

The Wild West, when train robberies happened! These outlaws rode fleet on horseback and took what they wanted; We need Sheriffs of all ages to help us ...  »

23 May

Club Regent Event Centre, 1425 Regent Ave. W., Winnipeg

May 23, 2026

Tickets Starting at $35.00

Tim Hicks is a 5-Time JUNO Award nominee, CCMA Award winner, with Multi Platinum selling singles and seventeen Top 10 radio hits (including the #1 singles “No Truck Song” ...  »

23 May

Rene Memorial Park , 6961 Sperling Ave, Burnaby

May 23, 2026

$20 - $300

Join us at the St. Francis De Sales’ 4th Annual Spring Fair! Pony rides, performances, games, inflatables plus food and drinks! Admission is FREE! But note the ...  »

24 May

FortWhyte Alive, 1961 McCreary Road, Winnipeg

May 24, 2026 To May 31, 2026

$55 - $65 + $15 Material Cost

Doug Mackie will take you down a road of chatter, stories and lessons where you discover the basics of carving your own diamond willow stick.  »

24 May

Oak Hammock Marsh, 1 Snow Goose Bay, Stonewall

May 24, 2026

$10.00 – $15.00 per person

Join this short interactive Guided Marsh Walk with of our nature interpreters. Some puppets may make an appearance.  »

24 May

Assiniboine Park Zoo & The Leaf, Winnipeg

May 24, 2026 To May 27, 2026

Ticketed

Celebrate and connect at Pride in the Park events at the Zoo and The Leaf! As a Rainbow Registered organization, we are proud to celebrate the diversity ...  »

24 May

Prairie Dog Central, 64099 Prairie Dog Trail, Winnipeg

May 24, 2026

$45

A relaxing ride down the tracks, no theme, no noise – bring a book, your headphones and enjoy the prairie summer air on a Sunday afternoon with a ...  »

26 May

Various Venues, Winnipeg

May 26, 2026 To June 7, 2026

Free

Join us in honoring and embracing the inclusive community that stands by LGBTTQ* (lesbian, gay, bisexual, transgender, two-spirit, and queer) individuals.  »

29 May

Canada Life Centre, 300 Portage Ave., Winnipeg

May 29, 2026 To May 30, 2026

(204) 926 - 5515

$49.95 - $89.95 + fees

Flatlander's Beer Festival is a unique public tasting event in Winnipeg. The two-day event has a wide range of incredible beers from some of the finest breweries ...  »

29 May

Red River Exhibition Park, 3977 Portage Avenue, Winnipeg

May 29, 2026 To May 31, 2026

Free

Where we bring finger licking good ribs, pulled pork, sausage, and more to Red River Exhibition Park!! We are excited to bring you, not only good food, ...  »

29 May

Assiniboia Downs, 3975 Portage Avenue, Winnipeg

May 29, 2026 To May 31, 2026

$5 (5 & under free)

Come hungry and dig into fall-off-the-bone ribs, smoky brisket, and all your BBQ favourites from top pitmasters. Kick back with live music, cold drinks, and a lively ...  »

29 May

Burton Cummings Theatre, 364 Smith St, Winnipeg

May 29, 2026

$51 and up

Rita Rudner, a house-filling favourite in Las Vegas since she opened as one of the hottest tickets in town in June 2000, is known for her epigrammatic one-liners. ...  »

30 May

Manitoba Canoe and Kayak Club, 80 Churchill Drive, Winnipeg

May 30, 2026

Free

The largest school dragon boat event in the country this festival is open to all schools across the province, with 50 teams coming to compete some as far ...  »

30 May

TBA, Winnipeg

May 30, 2026

General Admission $189

Storefront's Table For 1200 brings together architecture, design, and the culinary arts to create a spectacular 'pop-up' outdoor dining experience with entertainment and stimulating conversation in an absolutely ...  »

30 May

Memorial Park and Boulevard, 219 Memorial Blvd., Wpg

May 30, 2026 To May 31, 2026

204 8806352

Free

A vibrant celebration of Asian cultures, traditions, and cuisine. This exciting event will showcase the diverse flavors, sights, and sounds of Asia, bringing together communities for a ...  »

30 May

Various Venues, Winnipeg

May 30, 2026 To May 31, 2026

204.942.2663

Free

Celebrating the stories our buildings tell! On May 30th & 31st, 2026, buildings throughout Winnipeg and beyond will open their doors to the public for FREE! Take part ...  »

30 May

Burton Cummings Theatre, 364 Smith St, Winnipeg

May 30, 2026

$64 and up

Direct from Off-Broadway and London’s West End, the internationally acclaimed A Taste of Ireland Company returns with its flagship production — ‘A Taste of Ireland — The Irish ...  »

30 May

Royal Manitoba Theatre Centre - Mainstage, 174 Market Avenue, Winnipeg

May 30, 2026

$29.99 - $95.25

Daan (Tagalog for “the road”) is a vibrant celebration of musical theatre, lead by powerhouse performers Ma-Anne Dionisio and Stephanie Sy. This one night only concert blends ...  »

30 May

Royal Manitoba Theatre Centre - John Hirsch Mainstage, 174 Market Avenue, Winnipeg

May 30, 2026

$29.99 - $95.25

Daan (Tagalog for “the road”) is a vibrant celebration of musical theatre, led by powerhouse performers Ma-Anne Dionisio and Stephanie Sy. This one-night-only concert blends beloved Broadway ...  »

30 May

Children’s Museum, 45 Forks Market Road, Winnipeg

May 30, 2026 To September 7, 2026

Included with general museum admission

Ignite your inner scientist in Motion Mania – a thrilling 2,000 sq. ft. interactive journey into motion and energy created by the Ontario Science Centre.  »

30 May

Prairie Dog Central, 64099 Prairie Dog Trail, Winnipeg

May 30, 2026

Join Huntrix through their double lives as they seek their rivals, the Saja Boys. This chart topping animation sensation draws on elements of mythology, demonology and K-Pop.  »

31 May

Club Regent Event Centre, 1425 Regent Ave. W., Winnipeg

May 31, 2026

Tickets Starting at $25.00

The InClines’ “Sweet Dreams of Patsy Cline” is a musical celebration of the life and times of the legendary Patsy Cline. Through narration and song, The InClines ...  »

31 May

Manitoba Canoe and Kayak Centre, 80 Churchill Drive, Winnipeg

May 31, 2026

2047792441

Free for Spectators

Never Alone Cancer Foundation is proud to partner with the Manitoba Paddling Association to host one of the summer’s biggest events: The River City Dragon Boat ...  »

31 May

Canadian Museum for Human Rights, 85 Israel Asper Way, Winnipeg

May 31, 2026

$25 + Brunch extra

Make your morning shine bright! Come for a joyful brunch sprinkled with performances by local drag artists.  »

31 May

Red River Exhibition Park, 3977 Portage Avenue, Winnipeg

May 31, 2026

$13.33 - $25.71

Experience high-energy drag races, a full-throttle burnout competition, and a packed show-off area featuring some of the region’s best builds.   »

31 May

Prairie Dog Central, 64099 Prairie Dog Trail, Winnipeg

May 31, 2026

$55

The universe’s greatest superheroes will unite at the Prairie Dog Central Railway for this epic themed train ride featuring, Superman, Batman, Wonder Woman, Flash, & more!  »

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